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Aryl naproxen derivative high-valence iodine compound, preparation method and application thereof

A technology for aryl naproxen and derivatives, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of sulfonates, etc., can solve the problems of narrow application range, poor selectivity, lack of naproxen derivatives, etc. , to achieve the effect of concise and clear structure modification, high reactivity and easy preparation

Active Publication Date: 2020-11-17
WUYI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, common naproxen derivatives are modified on the naproxen aryl group by modifying the aliphatic chain hydrocarbon carboxyl group of naproxen or directly performing C-H activation on the naproxen aryl group, but this method Usually requires the use of transition metal catalysts, poor selectivity, narrow scope of application
The naproxen-like drug molecules obtained from the reactions reported above are very limited, which is not conducive to the construction of a huge naproxen-like drug library.
[0004] In summary, the synthesis of naproxen derivatives lacks an effective method with simple preparation process, good selectivity and wide application range.

Method used

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  • Aryl naproxen derivative high-valence iodine compound, preparation method and application thereof
  • Aryl naproxen derivative high-valence iodine compound, preparation method and application thereof
  • Aryl naproxen derivative high-valence iodine compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A kind of preparation of hypervalent iodine trifluoromethanesulfonate of phenylnaproxen methyl ester comprises the following steps:

[0041] 1) Add 10 mmol of hydroxy (p-toluenesulfonyloxy) iodobenzene to a mixed solution of 80 mL of dichloromethane and 8 mL of 2,2,2-trifluoroethanol, then add 10 mmol of naproxen methyl ester compound, and cool the reaction solution After reaching 0°C, 10 mmol of trimethylsilyl trifluoromethanesulfonate was added dropwise, and then reacted at room temperature for 1 h.

[0042] 2) After the reaction was completed, the solvent was distilled off under reduced pressure, and diethyl ether was added to stir and precipitate to obtain a white solid product with a yield of 88%.

[0043] NMR characterization of hypervalent iodine trifluoromethanesulfonate of phenylnaproxen methyl ester as follows figure 1 Shown: 1H NMR (400MHz, CHLOROFORM-D) δ8.10 (d, J = 9.0Hz, 1H), 7.95 (d, J = 8.7Hz, 1H), 7.86 (d, J = 7.5Hz, 2H), 7.76(s,1H),7.63(d,J=7.1Hz,1H...

Embodiment 2

[0045]A kind of preparation of hypervalent iodine trifluoromethanesulfonate of 4-methylphenylnaproxen methyl ester comprises the following steps:

[0046] 1) In a 250mL round-bottomed flask, dissolve 10mmol of 4-methyliodobenzene in 100mL of dichloromethane, add 10mmol of m-chloroperoxybenzoic acid under stirring conditions, then add 10mmol of toluenesulfonic acid monohydrate, at room temperature Stir at low temperature for 30 minutes. After the reaction is complete, spin the solvent to dryness, add 150 mL of ether, and stir thoroughly for 30 minutes to form a precipitate. After filtration and drying in vacuum, the yield of hydroxy(p-toluenesulfonyloxy)4-methyliodobenzene was 98%.

[0047] 2) In a 250mL round bottom flask, add 8mmol of the hydroxyl group (p-toluenesulfonyloxy) obtained in step 1) into a mixed solution of 65mL of dichloromethane and 6.5mL of 2,2,2-trifluoroethanol or hexafluoroisopropanol 8 mmol of naproxen methyl ester compound was then added, the reaction so...

Embodiment 3

[0051] A kind of preparation of hypervalent iodine trifluoromethanesulfonate of 2.4.6-trimethylphenylnaproxen methyl ester, comprises the following steps:

[0052] 1) In a 250mL round bottom flask, dissolve 10mmol of iodine in 80mL of dichloromethane, add 20mmol of mesitylene under stirring conditions, then add 30mmol of m-chloroperoxybenzoic acid and 20mmol of p-toluenesulfonic acid monohydrate, The reaction was carried out at room temperature for 1 hour. After the reaction was completed, the solvent was spin-dried, and 150 mL of diethyl ether was added, and stirred thoroughly for 30 minutes to form a precipitate. After filtration and drying in vacuo, the yield of hydroxy(p-toluenesulfonyloxy)-me-trimethyliodobenzene was 97%.

[0053] 2) In a 250mL round-bottomed flask, add 8mmol of hydroxy(p-toluenesulfonyloxy)s-trimethyliodobenzene obtained in step 1) into 65mL of dichloromethane and 2,2,2-trifluoroethanol or hexafluoroiso To a mixed solution of 6.5 mL of propanol, 8 mmol ...

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Abstract

The invention discloses an aryl naproxen derivative high-valence iodine compound, a preparation method and application thereof, wherein a series of naproxen derivatives are prepared through preparation and derivatization of naproxen high-valence iodine compounds. The compound can realize nucleophilic substitution reaction of specific sites on naproxen molecule aryl, so that the purpose of modifying the drug molecules is achieved, and the variety of the drug molecules is expanded. The invention also provides a preparation method of the compound, wherein the method comprises the following steps:synthesizing a naproxen derivative, and carrying out anion ligand exchange reaction on the naproxen derivative and a koser reagent derivative or an aryl iododiacetic acid compound to prepare the arylnaproxen derivative high-valence iodine compound. The high-valence iodine compound can perform concise and clear structural modification on naproxen molecular aryl, realizes rapid synthesis of structural diversity of drug molecules through accurate modification at specific sites, is convenient for rapid construction of a huge drug-like compound library, and greatly promotes the discovery processof naproxen drug active primers.

Description

technical field [0001] The invention relates to an aryl naproxen derivative hypervalent iodine compound and its preparation method and application, that is, a series of naproxen derivatives are prepared through the preparation and derivation of a naproxen hypervalent iodine compound, belonging to the technical field of organic synthesis chemistry . Background technique [0002] Naproxen is an arylpropionic acid non-steroidal anti-inflammatory analgesic (NSAIDs), which can significantly inhibit the synthesis of prostaglandins, and can stabilize lysosome activity, and has strong anti-inflammatory, anti-rheumatic, antipyretic and analgesic effects effect. These drugs play an indispensable role in non-steroidal anti-inflammatory analgesics because of their strong effects and small toxic and side effects. Therefore, the field of synthesis of such compounds needs to develop an efficient, simple and economical method. [0003] So far, common naproxen derivatives are modified on ...

Claims

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Application Information

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IPC IPC(8): C07C309/66C07C69/734C07C303/26C07C71/00C07C67/307C07C67/11C07C69/78
CPCC07C309/66C07C69/734C07C303/26C07C71/00C07C67/307C07C67/11C07C69/78
Inventor 陈超周均涂伯榕贺浩陈泗林郭盛柱吴盼盼
Owner WUYI UNIV
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